Uncovering Nonconventional and Conventional Hydrogen Bonds in Oligosaccharides through NMR Experiments and Molecular Modeling: Application to Sialyl Lewis-X

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• 作者：Marcos D. Battistel ; Hugo F. Azurmendi ; Martin Frank ; Dar贸n I. Freedberg
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：October 28, 2015
• 年：2015
• 卷：137
• 期：42
• 页码：13444-13447
• 全文大小：383K
• ISSN：1520-5126

文摘

We describe the direct NMR detection of a C鈥揌路路路O nonconventional hydrogen bond (Hbond) and provide experimental and theoretical evidence for conventional Hbonds in the pentasaccharide sialyl Lewis-X (sLe^X-5) between 5 and 37 掳C in water. Extensive NMR structural studies together with molecular dynamics simulations offer strong evidence for significant local dynamics in the Le^X core and for previously undetected conventional Hbonds in rapid equilibrium that modulate structure. These NMR studies also showed temperature-dependent ¹H and ¹³C line broadening. The resulting model emerging from this study is more complex than a simple rigid core description of Le^X-like molecules and improves our understanding of stabilizing interactions in glycans.